The present invention relates to phosphorus-containing benzoyl derivatives of the formula I 
in which:
X is oxygen or sulfur;
R1,R2 are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, mercapto, C1-C6-alkylthio, C3-C6-alkenylthio, C3-C6-alkynylthio, amino, C1-C6-alkylamino, di(C1-C6-alkyl)amino, (C1-C6-alkoxy)(C1-C6-alkyl)amino, (C3-C6-alkenyl)(C1-C6-alkyl)amino, (C3-C6-alkynyl)(C1-C6-alkyl)amino, di(C3-C6-alkenyl)amino or di(C3-C6-alkynyl)amino, where the abovementioned alkyl, alkenyl or alkynyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, di(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, phenyl or heterocyclyl, where the the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
xe2x80x83are phenyl or phenoxy which may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl; or
R1 and R2 together form an xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94NR5xe2x80x94(CH2)mxe2x80x94NR5xe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94NR5xe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94NR5xe2x80x94, xe2x80x94(CH2)nxe2x80x94Oxe2x80x94, xe2x80x94(CH2)nxe2x80x94Sxe2x80x94 or xe2x80x94(CH2)nxe2x80x94NR5 chain which may carry one to three radicals from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or phenyl which is unsubstituted or partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl; or
R1 and R2 together form a xe2x80x94(CH2)p chain which may be interrupted by oxygen, sulfur or NR5 and/or may carry one to three radicals from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or phenyl which is unsubstituted or partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R3 is hydrogen, nitro, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, aminosulfonyl, C1-C6-alkylaminosulfonyl, di(C1-C6-alkyl)aminosulfonyl, (C1-C6-alkylsulfonyl)amino, (C1-C6-haloalkylsulfonyl)amino, Nxe2x80x94(C1-C6-alkyl)xe2x80x94Nxe2x80x94(C1-C6-alkylsulfonyl)amino, Nxe2x80x94(C1-C6-alkyl)xe2x80x94Nxe2x80x94(C1-C6-haloalkylsulfonyl)amino, xe2x80x94P(xe2x95x90X)R1R2, phenyl or heterocyclyl, where the two last-mentioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R4 is nitro, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl or C1-C6-alkylsulfonyl;
R5 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy;
l is 0, 1 or 2;
m is 2, 3 or 4;
n is 3, 4 or 5;
p is 4, 5 or 6;
Q is a radical of the formula Q1, Q2, Q3 or Q4 
R6 is hydroxyl, mercapto, halogen, OR13, SR13, SOR14, SO2R14, OSO2R14, POR15R16, OPR15R16, OPOR15R16, OPSR15R16, NR17R18, ONR18R19, N-bonded heterocyclyl or Oxe2x80x94(N-bonded heterocyclyl), where the heterocyclyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R7,R9,R11 are hydrogen, nitro, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, di(C1-C6-alkoxy)methyl, di(C1-C6-alkylthio)methyl, (C1-C6-alkoxy)(C1-C6-alkylthio)methyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl or C1-C6-haloalkoxycarbonyl;
R8,R10,R12 are hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio or C1-C6-alkoxycarbonyl; or
R7 and R8 or R9 and R10 or R11 and R12 together form an xe2x80x94Oxe2x80x94(CH2)uxe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)uxe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)uxe2x80x94Sxe2x80x94, xe2x80x94Oxe2x80x94(CH2)vxe2x80x94 or xe2x80x94Sxe2x80x94(CH2)v chain which may be substituted by one to three radicals from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
R7 and R8 or R9 and R10 or R11 and R12 together form a xe2x80x94(CH2)w chain which may be interrupted by oxygen or sulfur and/or may be substituted by one to four radicals from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
R7 and R8 or R9 and R10 or R11 and R12 together form a methylidene group which may be substituted by one to two radicals from the following group:
halogen, hydroxyl, formyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl or C1-C6-haloalkylsulfonyl; or
R7 and R8 or R9 and R10 or R11 and R12 together with the carbon atom to which they are attached form a carbonyl group; or
R7 and R9 or R9 and R11 or R7 and R11 together form a xe2x80x94(CH2)v chain which may be substituted by one to three radicals from the following group:
halogen, C1-C6-alkyl, C1-C6-alkoxy, hydroxyl or C1-C6-alkoxycarbonyl;
R13 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C1-C20-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-alkylcarbonyl-C1-C6-alkyl or C1-C6-alkoxyimino-C1-C6-alkyl, where the abovementioned alkyl and cycloalkyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, di(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxy-C1-C4-alkoxycarbonyl, di(C1-C4-alkyl)amino-C1-C4-alkoxycarbonyl, hydroxycarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
is phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenylaminocarbonyl or heterocyclylaminocarbonyl, where the phenyl and the heterocyclyl radical of the 8 last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R14,R15, R16 are C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, hydroxyl, C1-C6-alkoxy, amino, C1-C6-alkylamino, C1-C6-haloalkylamino, di(C1-C6-alkyl)amino or di(C1-C6-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, di(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
are phenyl, heterocyclyl, phenoxy or heterocyclyloxy, where the phenyl and the heterocyclyl radical of the last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R17 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-halogenalkynyl, C3-C6-cycloalkyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy or C3-C6-alkynyloxy, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals from the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio or di(C1-C4-alkyl)amino;
is phenyl, heterocyclyl, phenyl-C1-C6-alkyl or heterocyclyl-C1-C6-alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R18, R19 are C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C1-C6-alkylcarbonyl;
u is 2 to 4;
v is 1 to 5;
w is 2 to 5;
R20 is a radical as mentioned under R6;
R21 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, hydroxyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
R22 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio or C1-C6-haloalkylthio;
R23 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl or C3-C6-halocycloalkyl;
R24 is hydrogen, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, hydroxycarbonyl or cyano;
R25 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl or C3-C6-halocycloalkyl;
and their agriculturally useful salts.
Moreover, the invention relates to the processes and intermediates for preparing compounds of the formula I, compositions comprising them and to the use of the compounds of the formula I and of the compositions comprising them for controlling pests.
Herbicidally effective phosphorothionoamidates are disclosed in the literature, for example in DE-A 22 60 705 and DE-A 21 66 729. Furtheermore, U.S. Pat. No. 3,775,057 describes pyridinylphosphonates.
Likewise, substituted benzoylisoxazoles or -pyrazoles and substituted 2-phenylcyclohexane-1,3-diones or 1-phenyl-2-cyanoalkane-1,3-diones are disclosed, for example, in EP-A 418 175, EP-A 609 797, WO 96/26 192, WO 96/26 206, EP-A 203 428, U.S. Pat. No. 4,780,127, EP-A 315 075 and EP-A 625 505.
However, the herbicidal properties of the prior art compounds and their compatibility with crop plants are not entirely satisfactory. It is an object of the present invention to provide novel, in particular herbicidally effective compounds having improved properties.
We have found that this object is achieved by the phosphorus-containing benzoyl derivatives of the formula I and their herbicidal action.
Furthermore, we have found herbicidal compositions comprising the compounds I and having very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they exist in the form of enantiomers or diastereomer mixtures.
The invention provides both the pure enantiomers or diastereomers and mixtures thereof.
The compounds of the formula I can also be present in the form of their agriculturally useful salts, the type of salt generally being immaterial. In general, the salts of those cations or the acid addition salts of those acids are suitable whose cations and anions, respectively, do not affect the herbicidal action of the compounds I negatively.
Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, the alkaline earth metals, preferably calcium and magnesium, and the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
The organic molecular moieties mentioned for the substituents R1-R25 or as radicals on phenyl and heterocyclyl radicals are collective terms for individual lists of the individual group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, alkylamino, dialkylamino, haloalkylamino, di(haloalkyl)amino, N-alkoxy-N-alkylamino, N-alkylsulfonylamino, N-haloalkylsulfonylamino, N-alkyl-N-alkylsulfonylamino, N-alkyl-N-haloalkylsulfonylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, dialkoxymethyl, dialkylthiomethyl, (alkoxy)(alkylthio)methyl, alkylcarbonylalkyl, alkoxyiminoalkyl, alkoxycarbonyloxy, phenylalkyl, heterocyclylalkyl, dialkylaminoalkoxycarbonyl, alkoxyalkoxycarbonyl, alkenylcarbonyl, N-alkenyl-N-alkylamino, dialkenylamino, alkynylcarbonyl, N-alkynyl-N-alkylamino, dialkynylamino, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkenylthio, alkynyloxy and alkynylthio moieties can be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The term halogen represents in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are:
C1-C4-alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;
C1-C6-alkyl, and the alkyl moieties of C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-alkoxyimino-C1-C6-alkyl, Nxe2x80x94(C3-C6-alkenyl)-Nxe2x80x94(C1-C6-alkyl)amino, Nxe2x80x94(C3-C6-alkynyl)-Nxe2x80x94(C1-C6-alkyl)amino, phenyl-C1-C6-alkyl, Nxe2x80x94(C1-C6-alkyl)-Nxe2x80x94(C1-C6-alkylsulfonyl)amino, Nxe2x80x94(C1-C6-alkyl)-Nxe2x80x94(C1-C6-haloalkylsulfonyl)amino, heterocyclyl-C1-C6-alkyl: C1-C4-alkyl as mentioned above, and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-3-methylpropyl;
C1-C4-haloalkyl: a C1-C4-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluorpmethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;
C1-C6-haloalkyl, and the haloalkyl moieties of C1-C6-haloalkylamino, di(C1-C6-haloalkyl)amino: C1-C4-haloalkyl, as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;
C1-C4-alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;
C1-C6-alkoxy, and the alkoxy moieties of di(C1-C6-alkoxy)methyl, (C1-C6-alkoxy)(C1-C6-alkylthio)methyl, C1-C6-alkoxyimino-C1-C6-alkyl and Nxe2x80x94(C1-C6-alkoxy)-Nxe2x80x94(C1-C6-alkyl)amino: C1-C4-alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
C1-C4-haloalkoxy: a C1-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;
C1-C6-haloalkoxy, and the haloalkoxy moieties of C1-C6-haloalkoxy-C1-C6-alkyl: C1-C4-haloalkoxy as mentioned above, and also, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;
C1-C4-alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio;
C1-C6-alkylthio, and the alkylthio moieties of C1-C6-alkylthio-C1-C6-alkyl, di(C1-C6-alkylthio)methyl and (C1-C6-alkoxy)(C1-C6-alkylthio)methyl: C1-C4-alkylthio as mentioned above, and also, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;
C1-C6-haloalkylthio: a C1-C6-alkylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio, nonafluorobutylthio, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio;
C1-C4-alkylsulfinyl (C1-C4-alkyl-S(xe2x95x90O)xe2x80x94): for example methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1,1-dimethylethylsulfinyl;
C1-C6-alkylsulfinyl and the alkylsulfinyl radicals of C1-C6-alkylsulfinyl-C1-C6-alkyl: C1-C4-alkylsulfinyl, as mentioned above, and also, for example, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethyl propylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl;
C1-C6-haloalkylsulfinyl: a C1-C6-alkylsulfinyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl, 1-(fluoromethyl)-2-fluoroethylsulfinyl, 1-(chloromethyl)-2-chloroethylsulfinyl, 1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl, nonafluorobutylsulfinyl, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chaorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl;
C1-C4-alkylsulfonyl (C1-C4-alkyl-S(xe2x95x90O)2xe2x80x94): for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropyl sulfonyl or 1,1-dimethylethylsulfonyl;
C1-C6-alkylsulfonyl, and the alkylsulfonyl radicals of C1-C6-alkylsulfonyl-C3-C6-alkyl, C1-C6-alkylsulfonylamino and Nxe2x80x94(C4-C6-alkyl)-Nxe2x80x94(C1-C6-alkylsulfonyl)amino: C1-C4-alkylsulfonyl as mentioned above, and also pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl;
C1-C6-haloalkylsulfonyl, and the haloalkylsulfonyl radicals of Nxe2x80x94(C1-C6-haloalkylsulfonyl)amino and Nxe2x80x94(C1-C6-alkyl)-Nxe2x80x94(C1-C6-haloalkylsulfonyl)amino: a C1-6-alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl;
C1-C6-alkylamino, and the alkylamino radicals of (C1-C6-alkoxy)(C1-C6-alkyl)amino: for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;
(C1-C6-alkylamino)sulfonyl: for example methylaminosulfonyl, ethylaminosulfonyl, propylaminosulfonyl, 1-methylethylaminosulfonyl, butylaminosulfonyl, 1-methylpropylaminosulfonyl, 2-methylpropylaminosulfonyl, 1,1-dimethylethylaminosulfonyl, pentylaminosulfonyl, 1-methylbutylaminosulfonyl, 2-methylbutylaminosulfonyl, 3-methylbutylaminosulfonyl, 2,2-dimethylpropylaminosulfonyl, 1-ethylpropylaminosulfonyl, hexylaminosulfonyl, 1,1-dimethylpropylaminosulfonyl, 1,2-dimethylpropylaminosulfonyl, 1-methylpentylaminosulfonyl, 2-methylpentylaminosulfonyl, 3-methylpentylaminosulfonyl, 4-methylpentylaminosulfonyl, 1,1-dimethylbutylaminosulfonyl, 1,2-dimethylbutylaminosulfonyl, 1,3-dimethylbutylaminosulfonyl, 2,2-dimethylbutylaminosulfonyl, 2,3-dimethylbutylaminosulfonyl, 3,3-dimethylbutylaminosulfonyl, 1-ethylbutylaminosulfonyl, 2-ethylbutylaminosulfonyl, 1,1,2-trimethylpropylaminosulfonyl, 1,2,2-trimethylpropylaminosulfonyl, 1-ethyl-1-methylpropylaminosulfonyl or 1-ethyl-2-methylpropylaminosulfonyl;
di(C1-C6-alkyl)aminosulfonyl: for example N,N-dimethylaminosulfonyl, N,N-diethylaminosulfonyl, N,N-di(1-methylethyl)aminosulfonyl, N,N-dipropylaminosulfonyl, N,N-dibutylaminosulfonyl, N,N-di(1-methylpropyl)aminosulfonyl, N,N-di(2-methylpropyl)aminosulfonyl, N,N-di(1,1-dimethylethyl)aminosulfonyl, N-ethyl-N-methylaminosulfonyl, N-methyl-N-propylaminosulfonyl, N-methyl-N-(1-methylethyl)aminosulfonyl, N-butyl-N-methylaminosulfonyl, N-methyl-N-(1-methylpropyl)aminosulfonyl, N-methyl-N-(2-methylpropyl)aminosulfonyl, N-(1,1-dimethylethyl)-N-methylaminosulfonyl, N-ethyl-N-propylaminosulfonyl, N-ethyl-N-(1-methylethyl)aminosulfonyl, N-butyl-N-ethylaminosulfonyl, N-ethyl-N-(1-methylpropyl)aminosulfonyl, N-ethyl-N-(2-methylpropyl)aminosulfonyl, N-ethyl-N-(1,1-dimethylethyl)aminosulfonyl, N-(1-methylethyl)-N-propylaminosulfonyl, N-butyl-N-propylaminosulfonyl, N-(1-methylpropyl)-N-propylaminosulfonyl, N-(2-methylpropyl)-N-propylaminosulfonyl, N-(1,1-dimethylethyl)-N-propylaminosulfonyl, N-butyl-N-(1-methylethyl)aminosulfonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminosulfonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminosulfonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminosulfonyl, N-butyl-N-(1-methylpropyl)aminosulfonyl, N-butyl-N-(2-methylpropyl)aminosulfonyl, N-butyl-N-(1,1-dimethylethyl)aminosulfonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminosulfonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminosulfonyl, N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminosulfonyl, N-methyl-N-pentylaminosulfonyl, N-methyl-N-(1-methylbutyl)aminosulfonyl, N-methyl-N-(2-methylbutyl)aminosulfonyl, N-methyl-N-(3-methylbutyl)aminosulfonyl, N-methyl-N-(2,2-dimethylpropyl)aminosulfonyl, N-methyl-N-(1-ethylpropyl)aminosulfonyl, N-methyl-N-hexylaminosulfonyl, N-methyl-N-(1,1-dimethylpropyl)aminosulfonyl, N-methyl-N-(1,2-dimethylpropyl)aminosulfonyl, N-methyl-N-(1-methylpentyl)aminosulfonyl, N-methyl-N-(2-methylpentyl)aminosulfonyl, N-methyl-N-(3-methylpentyl)aminosulfonyl, N-methyl-N-(4-methylpentyl)aminosulfonyl, N-methyl-N-(1,1-dimethylbutyl)aminosulfonyl, N-methyl-N-(1,2-dimethylbutyl)aminosulfonyl, N-methyl-N-(1,3-dimethylbutyl)aminosulfonyl, N-methyl-N-(2,2-dimethylbutyl)aminosulfonyl, N-methyl-N-(2,3-dimethylbutyl)aminosulfonyl, N-methyl-N-(3,3-dimethylbutyl)aminosulfonyl, N-methyl-N-(1-ethylbutyl)aminosulfonyl, N-methyl-N-(2-ethylbutyl)aminosulfonyl, N-methyl-N-(1,1,2-trimethylpropyl)aminosulfonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminosulfonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl, N-ethyl-N-pentylaminosulfonyl, N-ethyl-N-(1-methylbutyl)aminosulfonyl, N-ethyl-N-(2-methylbutyl)aminosulfonyl, N-ethyl-N-(3-methylbutyl)aminosulfonyl, N-ethyl-N-(2,2-dimethylpropyl)aminosulfonyl, N-ethyl-N-(1-ethylpropyl)aminosulfonyl, N-ethyl-N-hexylaminosulfonyl, N-ethyl-N-(1,1-dimethylpropyl)aminosulfonyl, N-ethyl-N-(1,2-dimethylpropyl)aminosulfonyl, N-ethyl-N-(1-methylpentyl )aminosulfonyl, N-ethyl-N-(2-methylpentyl)aminosulfonyl, N-ethyl-N-(3-methylpentyl)aminosulfonyl, N-ethyl-N-(4-methylpentyl)aminosulfonyl, N-ethyl-N-(1,1-dimethyl butyl)aminosulfonyl, N-ethyl-N-(1,2-dimethylbutyl)aminosulfonyl, N-ethyl-N-(1,3-dimethylbutyl)aminosulfonyl, N-ethyl-N-(2,2-dimethylbutyl)aminosulfonyl, N-ethyl-N-(2,3-dimethylbutyl)aminosulfonyl, N-ethyl-N-(3,3-dimethylbutyl)aminosulfonyl, N-ethyl-N-(1-ethylbutyl)aminosulfonyl, N-ethyl-N-(2-ethylbutyl)aminosulfonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminosulfonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminosulfonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl, N-propyl-N-pentylaminosulfonyl, N-butyl-N-pentylaminosulfonyl, N,N-dipentylaminosulfonyl, N-propyl-N-hexylaminosulfonyl, N-butyl-N-hexylaminosulfonyl, N-pentyl-N-hexylaminosulfonyl or N,N-dihexylaminosulfonyl;
di(C1-C4-alkyl)amino, and the dialkylamino radicals of di(C1-C4-alkyl)amino-C1-C4-alkoxycarbonyl: for example N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino, N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;
di(C1-C6-alkyl)amino: di(C1-C4-alkyl)amino as mentioned above, and also N,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino, N-ethyl-N-pentylamino, N-methyl-N-hexylamino or N-ethyl-N-hexylamino;
C1-C4-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1,1-dimethylethylcarbonyl;
C1-C6-alkylcarbonyl, and the alkylcarbonyl radicals of C1-C6-alkylcarbonyl-C1-C6-alkyl: C1-C4-alkylcarbonyl as mentioned above, and also, for example, pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;
C1-C20-alkylcarbonyl: C1-C6-alkylcarbonyl as mentioned above, and also heptylcarbonyl, octylcarbonyl, pentadecylcarbonyl or heptadecylcarbonyl;
C1-C6-haloalkylcarbonyl: a C1-C6-alkylcarbonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl, 1-(fluoromethyl)-2-fluoroethylcarbonyl, 1-(chloromethyl)-2-chloroethylcarbonyl, 1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl, nonafluorobutylcarbonyl, 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5-bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorohexylcarbonyl, 6-chlorohexylcarbonyl, 6-bromohexylcarbonyl or perfluorohexylcarbonyl;
C1-C4-alkoxycarbonyl, and the alkoxycarbonyl moieties of di(C1-C4-alkyl)amino-C1-C4-alkoxycarbonyl: for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;
(C1-C6-alkoxy)carbonyl, and the alkoxycarbonyl moieties of C1-C6-alkoxycarbonyloxy: (C1-C4-alkoxy)carbonyl as mentioned above, and also, for example, pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl;
C1-C6-haloalkoxycarbonyl: a C1-C6-alkoxycarbonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, bromodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2,2-difluoroethoxycarbonyl, 2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl, 2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 3,3,3-trichloropropoxycarbonyl, 2,2,3,3,3-pentafluoropropoxycarbonyl, heptafluoropropoxycarbonyl, 1-(2fluoromethyl)-2-fluoroethoxycarbonyl, 1-(chloromethyl)-2-chloroethoxycarbonyl, 1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl, 4-iodobutoxycarbonyl, 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6-fluorohexoxycarbonyl, 6-chlorohexoxycarbonyl or 6-bromohexoxycarbonyl;
(C1-C4-alkylamino)carbonyl: for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1,1-dimethylethylaminocarbonyl;
(C1-C6-alkylamino)carbonyl: (C1-C4-alkylamino)carbonyl as mentioned above, and also, for example, pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl or 1-ethyl-2-methylpropylaminocarbonyl;
di(C1-C4-alkyl)aminocarbonyl: for example N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-di(1-methylethyl)aminocarbonyl, N,N-dipropylaminocarbonyl, N,N-dibutylaminocarbonyl, N,N-di(1-methylpropyl)aminocarbonyl, N,N-di(2-methylpropyl)aminocarbonyl, N,N-di(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N-(1-methylpropyl)-N-propylaminocarbonyl, N-(2-methylpropyl)-N-propylaminocarbonyl, N-(1,1-dimethylethyl)-N-propylaminocarbonyl, N-butyl-N-(1-methylethyl)aminocarbonyl, N-(-methylethyl)-N-(1-methylpropyl)aminocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(2-methylethyl)aminocarbonyl, N-butyl-N-(1-methylpropyl)aminocarbonyl, N-butyl-N-(2-methylpropyl)aminocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;
C1-C6-alkoxy-C1-C6-alkyl: C1-C6-alkyl which is substituted by C1-C6-alkoxy as mentioned above, i.e., for example, methoxymethyl, ethoxymethyl, propoxymethyl, (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl, 4-(1,1-dimethylethoxy)butyl, 5-methoxypentyl, 5-ethoxypentyl, 6-methoxyhexyl or 6-ethoxyhexyl;
the C1-C4-alkoxy-C1-C4-alkoxy radical of C1-C4-alkoxy-C1-C4-alkoxycarbonyl: C1-C4-alkoxy which is substituted by C1-C4-alkoxy as mentioned above, i.e., for example, methoxymethoxy, ethoxymethoxy, propoxymethoxy, (1-methylethoxy)methoxy, butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, (1,1-dimethylethoxy)methoxy, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(propoxy)propoxy, 2-(1-methylethoxy)propoxy, 2-(butoxy)propoxy, 2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy, 2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy, 3-(propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy, 3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy, 3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy, 2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(butoxy)butoxy, 2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)butoxy, 3-(propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy, 3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy, 3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)-butoxy, 4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(butoxy)butoxy, 4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy or 4-(1,1-dimethylethoxy)butoxy;
C3-C6-alkenyl, and the alkenyl moieties of C3-C6-alkenylcarbonyl, C3-C6-alkenyloxy, C3-C6-alkenylthio, Nxe2x80x94(C3-C6-alkenyl)-Nxe2x80x94(C1-C6-alkyl)amino and di(C3-C6-alkenyl)amino: for example prop-2-en-1-yl, but-1-en-4-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, 2-buten-1-yl, 1-penten-3-yl, 1-penten-4-yl, 2-penten-4-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl;
C2-C6-alkenyl, and the alkenyl moieties of C2-C6-alkenylcarbonyl: C3-C6-alkenyl as mentioned above, and also ethenyl;
C3-C6-haloalkenyl: a C3-C6-alkenyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;
C3-C6-alkynyl, and the alkynyl moieties of C3-C6-alkynylcarbonyl, C3-C6-alkynyloxy, C3-C6-alkynylthio, Nxe2x80x94(C3-C6-alkynyl)-Nxe2x80x94(C1-C6-alkyl)amino and di(C3-C6-alkynyl)amino: for example propargyl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl;
C2-C6-alkynyl, and the alkynyl moieties of C2-C6-alkynylcarbonyl: C3-C6-alkynyl as mentioned above, and also ethynyl;
C3-C6-haloalkynyl: a C3-C6-alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;
C3-C6-cycloalkyl, and the cycloalkyl moieties of C3-C6-cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
C3-C6-halocycloalkyl: a C3-C6-cycloalkyl radical as mentioned above which may be partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 2,2-dichlorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 3-chlorocyclopent-1-yl, 3-fluorocyclopent-1-yl, 3-bromocyclopent-1-yl, 3,3-dichlorocyclopent-1-yl, 3,3-difluorocyclopent-1-yl, 4-chlorocyclohex-1-yl, 4-fluorocyclohex-1-yl, 4-bromocyclohex-1-yl, 4,4-dichlorocyclohex-1-yl or 4,4-difluorocyclohex-1-yl;
heterocyclyl, and the heterocyclyl moieties of heterocyclylcarbonyl, heterocyclyl-C1-C6-alkyl, heterocyclyloxy, heterocyclylaminocarbonyl: a saturated, partially saturated or unsaturated 5- or 6-membered heterocyclic ring which is attached via carbon and contains one to four identical or different heteroatoms selected from the following group: oxygen, sulfur and nitrogen, i.e., for example, 5-membered rings such as:
tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 4,5-dihydrothien-2-yl, 4,5-dihydrothien-3-yl, 2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl, 2,5-dihydro-1H-pyrrol-2-yl, 2,5-dihydro-1H-pyrrol-3-yl, 4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl, 3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl, 3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl, pyrrol-3-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1,2-oxathiolan-3-yl, 1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl, 1,2-dithiolan-3-yl, 1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl, tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl, tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl, tetrahydrothiazol-5-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 4,5-dihydro-1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-1H-pyrazol-5-yl, 2,5-dihydro-1H-pyrazol-3-yl, 2,5-dihydro-1H-pyrazol-4-yl, 2,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, xcex943-1,2-dithiol-3-yl, xcex943-1,2-dithiol-4-yl, xcex943-1,2-dithiol-5-yl, 4,5-dihydro-1H-imidazol-2-yl, 4,5-dihydro-1H-imidazol-4-yl, 4,5-dihydro-1H-imidazol-5-yl, 2,5-dihydro-1H-imidazol-2-yl, 2,5-dihydro-1H-imidazol-4-yl, 2,5-dihydro-1H-imidazol-5-yl, 2,3-dihydro-1H-imidazol-2-yl, 2,3-dihydro-1H-imidazol-4-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl, 1,3-dioxol-4-yl, 1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl, 1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, 1,2,3-xcex942-oxadiazolin-4-yl, 1,2,3-xcex942-oxadiazolin-5-yl, 1,2,4-xcex944-oxadiazolin-3-yl, 1,2,4-xcex944-oxadiazolin-5-yl, 1,2,4-xcex942-oxadiazolin-3-yl, 1,2,4-xcex942-oxadiazolin-5-yl, 1,2,4-xcex943-oxadiazolin-3-yl, 1,2,4-xcex943-oxadiazolin-5-yl, 1,3,4-xcex942-oxadiazolin-2-yl, 1,3,4-xcex942-oxadiazolin-5-yl, 1,3,4-xcex943-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl, 1,2,4-xcex944-thiadiazolin-3-yl, 1,2,4-xcex944-thiadiazolin-5-yl, 1,2,4-xcex943-thiadiazolin-3-yl, 1,2,4-xcex943-thiadiazolin-5-yl, 1,2,4-xcex942-thiadiazolin-3-yl, 1,2,4-xcex942-thiadiazolin-5-yl, 1,3,4-xcex942-thiadiazolin-2-yl, 1,3,4-xcex942-thiadiazolin-5-yl, 1,3,4-xcex943-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl, 1,3,2-dioxathiolan-4-yl, 1,2,3-xcex942-triazolin-4-yl, 1,2,3-xcex942-triazolin-5-yl, 1,2,4-xcex942-triazolin-3-yl, 1,2,4-xcex942-triazolin-5-yl, 1,2,4-xcex943-triazolin-3-yl, 1,2,4-xcex943-triazolin-5-yl, 1,2,4-xcex941-triazolin-2-yl, 1,2,4-triazolin-3-yl, 3H-1,2,4-dithiazol-5-yl, 2H-1,3,4-dithiazol-5-yl, 2H-1,3,4-oxathiazol-5-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4,-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl, 1,2,3-triazol-4-yl, 1,2,4-triazol-3-yl, tetrazol-5-yl,
6-membered rings such as:
tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl, 2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl, 1,2,3,4-tetrahydropyridin-5-yl, 1,2,3,4-tetrahydropyridin-4-yl, 1,2,3,4-tetrahydropyridin-3-yl, 1,2,3,4-tetrahydropyridin-2-yl, 2H-5,6-dihydropyran-2-yl, 2H-5,6-dihydropyran-3-yl, 2H-5,6-dihydropyran-4-yl, 2H-5,6-dihydropyran-5-yl, 2H-5,6-dihydropyran-6-yl, 2H-5,6-dihydrothiopyran-2-yl, 2H-5,6-dihydrothiopyran-3-yl, 2H-5,6-dihydrothiopyran-4-yl, 2H-5,6-dihydrothiopyran-5-yl, 2H-5,6-dihydrothiopyran-6-yl, 1,2,5,6-tetrahydropyridin-2-yl, 1,2,5,6-tetrahydropyridin-3-yl, 1,2,5,6-tetrahydropyridin-4-yl, 1,2,5,6-tetrahydropyridin-5-yl, 1,2,5,6-tetrahydropyridin-6-yl, 2,3,4,5-tetrahydropyridin-2-yl, 2,3,4,5-tetrahydropyridin-3-yl, 2,3,4,5-tetrahydropyridin-4-yl, 2,3,4,5-tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl, 4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl, 4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl, 1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridin-2-yl, 1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl, 1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6-yl, 3,4-dihydropyridin-2-yl, 3,1-dihydropyridin-3-yl, 3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl, 3,4-dihydropyridin-6-yl, 2,5-dihydropyridin-2-yl, 2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl, 2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl, 2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl, 2,3-dihydropyridin-4-yl, 2,3-dihydropyridin-5-yl, 2,3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithian-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, 1,2-dithian-3-yl, 1,2-dithian-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-4-yl, tetrahydro-1,3-oxazin-5-yl, tetrahydro-1,3-oxazin-6-yl, tetrahydro-1,3-thiazin-2-yl, tetrahydro-1,3-thiazin-4-yl, tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6-yl, tetrahydro-1,4-thiazin-2-yl, tetrahydro-1,4-thiazin-3-yl, tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl, tetrahydro-1,2-oxazin-3-yl, tetrahydro-1,2-oxazin-4-yl, tetrahydro-1,2-oxazin-5-yl, tetrahydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-oxazin-3-yl, 2H-5,6-dihydro-1,2-oxazin-4-yl, 2H-5,6-dihydro-1,2-oxazin-5-yl, 2H-5,6-dihydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-thiazin-3-yl, 2H-5,6-dihydro-1,2-thiazin-4-yl, 2H-5,6-dihydro-1,2-thiazin-5-yl, 2H-5,6-dihydro-1,2-thiazin-6-yl, 4H-5,6-dihydro-1,2-oxazin-3-yl, 4H-5,6-dihydro-1,2-oxazin-4-yl, 4H-5,6-dihydro-1,2-oxazin-5-yl, 4H-5,6-dihydro-1,2-oxazin-6-yl, 4H-5,6-dihydro-1,2-thiazin-3-yl, 4H-5,6-dihydro-1,2-thiazin-4-yl, 4H-5,6-dihydro-1,2-thiazin-5-yl, 4H-5,6-dihydro-1,2-thiazin-6-yl, 2H-3,6-dihydro-1,2-oxazin-3-yl, 2H-3,6-dihydro-1,2-oxazin-4-yl, 2H-3,6-dihydro-1,2-oxazin-5-yl, 2H-3,6-dihydro-1,2-oxazin-6-yl, 2H-3,6-dihydro-1,2-thiazin-3-yl, 2H-3,6-dihydro-1,2-thiazin-4-yl, 2H-3,6-dihydro-1,2-thiazin-5-yl, 2H-3,6-dihydro-1,2-thiazin-6-yl, 2H-3,4-dihydro-1,2-oxazin-3-yl, 2H-3,4-dihydro-1,2-oxazin-4-yl, 2H-3,4-dihydro-1,2-oxazin-5-yl, 2H-3,4-dihydro-1,2-oxazin-6-yl, 2H-3,4-dihydro-1,2-thiazin-3-yl, 2H-3,4-dihydro-1,2-thiazin-4-yl, 2H-3,4-dihydro-1,2-thiazin-5-yl, 2H-3,4-dihydro-1,2-thiazin-6-yl, 2,3,4,5-tetrahydropyridazin-3-yl, 2,3,4,5-tetrahydropyridazin-4-yl, 2,3,4,5-tetrahydropyridazin-5-yl, 2,3,4,5-tetrahydropyridazin-6-yl, 3,4,5,6-tetrahydropyridazin-3-yl, 3,4,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-3-yl, 1,2,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-5-yl, 1,2,5,6-tetrahydropyridazin-6-yl, 1,2,3,6-tetrahydropyridazin-3-yl, 1,2,3,6-tetrahydropyridazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-5-yl, 4H-5,6-dihydro-1,3-oxazin-6-yl, 4H-5,6-dihydro-1,3-thiazin-2-yl, 4H-5,6-dihydro-1,3-thiazin-4-yl, 4H-5,6-dihydro-1,3-thiazin-5-yl, 4H-5,6-dihydro-1,3-thiazin-6-yl, 3,4,5-6-tetrahydropyrimidin-2-yl, 3,4,5,6-tetrahydropyrimidin-4-yl, 3,4,5,6-tetrahydropyrimidin-5-yl, 3,4,5,6-tetrahydropyrimidin-6-yl, 1,2,3,4-tetrahydropyrazin-2-yl, 1,2,3,4-tetrahydropyrazin-5-yl, 1,2,3,4-tetrahydropyrimidin-2-yl, 1,2,3,4-tetrahydropyrimidin-4-yl, 1,2,3,4-tetrahydropyrimidin-5-yl, 1,2,3,4-tetrahydropyrimidin-6-yl, 2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3-yl, 2,3-dihydro-1,4-thiazin-5-yl, 2,3-dihydro-1,4-thiazin-6-yl, 2H-1,2-oxazin-3-yl, 2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl, 2H-1,2-oxazin-6-yl, 2H-1,2-thiazin-3-yl, 2H-1,2-thiazin-4-yl, 2H-1,2-thiazin-5-yl, 2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl, 4H-1,2-oxazin-4-yl, 4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl, 4H-1,2-thiazin-3-yl, 4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl, 4H-1,2-thiazin-6-yl, 6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl, 6H-1,2-oxazin-5-yl, 6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl, 6H-1,2-thiazin-4-yl, 6H-1,2-thiazin-5-yl, 6H-1,2-thiazin-6-yl, 2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl, 2H-1,3-oxazin-6-yl, 2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl, 2H-1,3-thiazin-5-yl, 2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl, 4H-1,3-oxazin-4-yl, 4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl, 4H-1,3-thiazin-2-yl, 4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl, 4H-1,3-thiazin-6-yl, 6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl, 2H-1,4-oxazin-2-yl, 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl, 2H-1,4-oxazin-6-yl, 2H-1,4-thiazin-2-yl, 2H-1,4-thiazin-3-yl, 2H-1,4-thiazin-5-yl, 2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl, 4H-1,4-oxazin-3-yl, 4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl, 1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl, 1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl, 1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl, 1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl, 1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl, 1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl, 1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl, 3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl or 3,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,4,5-tetrazin-3-yl;
where, if appropriate, the sulfur of the abovementioned heterocycles can oxidized to Sxe2x95x90O or S(xe2x95x90O)2;
and where a bicyclic ring system may be formed with a fused-on phenyl ring or a C3-C6-carbocycle or with a further 5- to 6-membered heterocycle.
N-bonded heterocyclyl: a saturated, partially saturated or unsaturated 5- or 6-membered heterocyclic ring which is attached via nitrogen and contains at least one nitrogen and, if appropriate, one to three identical or different heteroatoms selected from the following group: oxygen, sulfur or nitrogen, i.e., for example
N-bonded 5-membered rings such as:
tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl, 2,5-dihydro-1H-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl, tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl, 4,5-dihydro-1H-pyrazol-1-yl, 2,5-dihydro-1H-pyrazol-1-yl, 2,3-dihydro-1H-pyrazol-1-yl, 2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl, 4,5-dihydro-1H-imidazol-1-yl, 2,5-dihydro-1H-imidazol-1-yl, 2,3-dihydro-1H-imidazol-1-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,4-xcex944-oxadiazolin-2-yl, 1,2,4-xcex942-oxadiazolin-4-yl, 1,2,4-xcex943-oxadiazolin-2-yl, 1,3,4-xcex942-oxadiazolin-4-yl, 1,2,4-xcex945-thiadiazolin-2-yl, 1,2,4-xcex943-thiadiazolin-2-yl, 1,2,4-xcex942-thiadiazolin-4-yl, 1,3,4-xcex942-thiadiazolin-4-yl, 1,2,3-xcex942-triazolin-1-yl, 1,2,4-xcex942-triazolin-1-yl, 1,2,4-xcex942-triazolin-4-yl, 1,2,4-xcex943-triazolin-1-yl, 1,2,4-xcex941-triazolin-4-yl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, tetrazol-1-yl;
and N-bonded 6-membered rings such as:
piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl, 1,2-dihydropyridin-1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, hexahydropyridazin-1-yl, tetrahydro-1,3-oxazin-3-yl, tetrahydro-1,3-thiazin-3-yl, tetrahydro-1,4-thiazin-4-yl, tetrahydro-1,4-oxazin-4-yl, tetrahydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-thiazin-2-yl, 2H-3,6-dihydro-1,2-oxazin-2-yl, 2H-3,6-dihydro-1,2-thiazin-oxazin-2-yl, 2H-3,4-dihydro-1,2-thiazin-2-yl, 2,3,4,5-tetrahydropyridazin-2-yl, 1,2,5,6-tetrahydropyridazin-1-yl, 1,2,5,6-tetrahydropyridazin-2-yl, 1,2, 3,6-tetrahydropyridazin-1-yl, 3,4,5,6-tetrahydropyrimidin-3-yl, 1,2,3,4-tetrahydropyrazin-1-yl, 1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihydro-1,4-thiazin-4-yl, 2H-1,2-oxazin-2-yl, 2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl, 4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-1-yl, 1,4-dihydropyrazin-1-yl, 1,2-dihydropyrazin-1-yl, 1,4-dihydropyrimidin-1-yl or 3,4-dihydropyrimidin-3-yl, and
N-bonded cyclic imides such as:
phthalimide, tetrahydrophthalimide, succinimide, maleimide or glutarimide, and also 4-oxo-1,4-dihydropyridin-1-yl.
All phenyl rings or heterocyclyl radicals and all phenyl components in phenyl-C1-C6-alkyl, phenoxy, phenylcarbonyl and phenylaminocarbonyl or heterocyclyl components in heterocyclyl-C1-C6-alkyl, heterocyclyloxy, heterocyclylcarbonyl and heterocyclylaminocarbonyl are, unless stated otherwise, preferably unsubstituted or they carry one to three halogen atoms and/or one nitro group, one cyano radical and/or one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy substituents.
Suitable heterocycyl radicals are, in particular, 5-membered aromatic heterocycles, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, 1,2,4-triazol-3-yl or tetrazol-5-yl;
5-membered partially unsaturated heterocycles, for example 4,5-dihydro-1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrothiazol-2-yl or 4,5-dihydroimidazol-2-yl;
5-membered saturated heterocycles, for example tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl or 1,3-dithiolan-4-yl;
6-membered aromatic heterocycles, for example pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl or 1,2,4-triazin-6-yl;
6-membered partially unsaturated heterocycles, for example 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 2H-3,4-dihydrothiopyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl, 2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydrothiopyran-3-yl, 2H-3,4-dihydrothiopyran-2-yl, 4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-thiazin-2-yl or 3,4,5,6-tetrahydropyrimidin-2-yl;
6-membered saturated heterocycles, for example tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl, tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl, tetrahydro-1,4-thiazin-2-yl or tetrahydro-1,4-thiazin-3-yl.
The compounds of the formula I according to the invention where Q=Q1 are referred to as compounds of the formula Ia, compounds of the formula I where Q=Q2 are referred to as Ib, compounds of the formula I where Q=Q3 are referred to as Ic and compounds of the formula I where Q=Q4 are referred to as Id.
With respect to the use of the compounds of the formula I according to invention as herbicides, the variables preferably have the following meaning, in each case on their own or in combination:
X is oxygen or sulfur;
in particular oxygen;
R1, R2 are hydrogen, C1-C6-alkyl, hydroxyl, C1-C6-alkoxy, C1-C6-alkylthio, di(C1-C6-alkyl)amino, where the alkyl radicals of the five last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4-alkoxy, C1-C4-alkylsulfonyl or C1-C4-alkoxycarbonyl;
in particular hydrogen, C1-C4-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylbutyl or 2-methylbutyl, hydroxyl, C1-C4-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy or 2-methylbutoxy, C1-C4-alkylthio such as methylthio, ethylthio, propylthio or 1-methylethylthio, or di(C1-C4-alkyl)amino such as dimethylamino, diethylamino, dipropylamino, dibutylamino, N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-butylamino, N-ethyl-N-propylamino or N-ethyl-N-butylamino; or
R1 and R2 together form a Oxe2x80x94O(CH2)mxe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94NR5xe2x80x94(CH2)mxe2x80x94NR5xe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94NR5xe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94NR5xe2x80x94 or xe2x80x94(CH2)p chain which may carry one to three radicals from the following group: halogen, cyano, C1-C4-alkyl or C1-C4-alkoxycarbonyl; in particular, R1 and R2 together form a xe2x80x94Oxe2x80x94(CH2)mxe2x80x94O, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94S or xe2x80x94(CH2)p chain;
R3 is hydrogen, nitro, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, xe2x80x94P(xe2x95x90O)(C1-C4-alkyl)2 or xe2x80x94P(xe2x95x90O)(C1-C4-alkoxy)2; in particular nitro, halogen, C1-C4-alkyl such as methyl or ethyl, C1-C4-haloalkyl such as difluoromethyl or trifluoromethyl, C1-C4-alkoxy such as methoxy or ethoxy, C1-C4-haloalkoxy such as difluoromethoxy, trifluoromethoxy or chlorodifluoromethoxy, C1-C4-alkylthio such as methylthio or ethylthio, C1-C4-alkylsulfonyl such as methylsulfonyl or ethylsulfonyl, C1-C4-haloalkylsulfonyl such as difluoromethylsulfonyl, trifluoromethylsulfonyl or chlorodifluoromethylsulfonyl, xe2x80x94P(xe2x95x90O)(CH3)2, xe2x80x94P(xe2x95x90O)(CH2CH3)2, xe2x80x94P(xe2x95x90O)(OCH3)2 or xe2x80x94P(xe2x95x90O)(OCH2CH3)2;
R4 is halogen, such as chlorine or bromine, or C1-C4-alkyl, such as methyl or ethyl;
R5 is hydrogen or C1-C4-alkyl, such as methyl or ethyl;
l is 0 or 1;
m is 2, 3 or 4;
p is 4 or 5;
Q is a radical of the formula Q1, Q2, Q3 or Q4;
R6 is hydroxyl, mercapto, halogen, OR13, SR13, SO2R14, OSO2R14, OPOR15R16, OPR15R16, OPSR15R16, NR17R18, ONR18R19, N-bonded heterocyclyl or Oxe2x80x94(N-bonded heterocyclyl), where the heterocyclyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R7,R9,R11 are hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, di(C1-C6-alkoxy)methyl, di(C1-C6-alkylthio)methyl, (C1-C6-alkoxy)(C1-C6-alkylthio)methyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl or C1-C6-haloalkoxycarbonyl;
R8,R10,R12 are hydrogen or C1-C6-alkyl;
in particular hydrogen or C1-C4-alkyl, such as methyl or ethyl; or
R7 and R8 or R9 and R10 or R11 and R12 together form a xe2x80x94Oxe2x80x94(CH2)uxe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)uxe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)uxe2x80x94Sxe2x80x94, xe2x80x94Oxe2x80x94(CH2)vxe2x80x94 or xe2x80x94Sxe2x80x94(CH2)v chain which may be substituted by one to three radicals from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
R7 and R8 or R9 and R10 or R11 and R12 together form a xe2x80x94(CH2)w chain which may be interrupted by oxygen or sulfur and/or substituted by one to four radicals from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
R7 and R8 or R9 and R10 or R11 and R12 together with the carbon atoms to which they are attached form a carbonyl group; or
R7 and R9 or R9 and R11 or R7 and R11 together form a xe2x80x94(CH2)v chain which may be substituted by one to three radicals from the following group: halogen, C1-C6-alkyl, C1-C6-alkoxy, hydroxyl or C1-C6-alkoxycarbonyl;
R13 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-alkylcarbonyl-C1-C6-alkyl or C1-C6-alkoxyimino-C1-C6-alkyl, where the abovementioned alkyl and cycloalkyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, hydroxycarbonyl, di(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
is phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenylcarbonyl or heterocyclylcarbonyl, where the phenyl and the heterocyclyl radical of the 6 last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R14,R15, R16 are C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-cycloalkyl, hydroxyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino or di(C1-C6-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
are phenyl, heterocyclyl, phenoxy or heterocyclyloxy, where the phenyl and the heterocyclyl radical of the last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R17 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-cycloalkyl, C1-C6-alkoxy or C3-C6-alkenyloxy, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals from the following group:
cyano, C1-C4-alkoxy or C1-C4-alkylthio;
is phenyl, heterocyclyl, phenyl-C1-C6-alkyl or heterocyclyl-C1-C6-alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R18, R19 are C1-C6-alkyl or C3-C6-alkenyl;
u is from 2 to 4;
v is from 1 to 5;
w is from 2 to 5;
R20 is a radical as mentioned under R6;
R21 is hydrogen, C1-C6-alkyl or C1-C6-haloalkyl; in particular hydrogen or C1-C4-alkyl such as methyl, ethyl, propyl, 1-methyleth-1-yl or 1,1-dimethyleth-1-yl;
R22 is hydrogen or C1-C6-alkyl; in particular hydrogen or C1-C4-alkyl, such as methyl or ethyl;
R23 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl or C3-C6-halocycloalkyl; in particular C1-C6-alkyl or C3-C6-cycloalkyl; very preferably cyclopropyl;
R24 is hydrogen;
R25 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl or C3-C6-halocycloalkyl; in particular C1-C6-alkyl or C3-C6-cycloalkyl.
Particular preference is given to the compounds Ia especially the compounds Ia where the variables have the following meanings, in each case on their own or in combination:
R6 is hydroxyl, mercapto, halogen, OR13, SR13, SO2R14, OSO2R14, NR17R18, ONR18R19 or N-bonded heterocyclyl, where the heterocyclyl radical of the last-mentioned substituent may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R7,R9,R11 are hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, di(C1-C6-alkoxy)methyl, di(C1-C6-alkylthio)methyl, (C1-C6-alkoxy)(C1-C6-alkylthio)methyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyloxy, C1-C6-alkylthio or C1-C6-haloalkylthio;
R8,R10,R12 are hydrogen or C1-C6-alkyl;
in particular hydrogen or C1-C4-alkyl, such as methyl or ethyl; or
R9 and R10 together with the carbon to which they are attached form a carbonyl group; or
R7 and R11 together form a xe2x80x94(CH2)v chain which may be substituted by one to three C1-C4-alkyl radicals;
R13 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkylaminocarbonyl or C1-C6-alkylcarbonyl-C1-C6-alkyl, where the abovementioned alkyl or cycloalkyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, hydroxycarbonyl, di(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
is phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenylcarbonyl or heterocyclylcarbonyl, where the phenyl and the heterocyclyl radical of the 6 last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R14 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-cycloalkyl, hydroxyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino or di(C1-C6-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
are phenyl, heterocyclyl, phenoxy or heterocyclyloxy, where the phenyl and the heterocyclyl radical of the last-mentioned substituents may be partially or fully halogenated and/or carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R17 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-cycloalkyl, C1-C6-alkoxy or C3-C6-alkenyloxy, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals from the following group:
cyano, C1-C4-alkoxy or C1-C4-alkylthio;
is phenyl, heterocyclyl, phenyl-C1-C6-alkyl or heterocyclyl-C1-C6-alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R18, R19 are C1-C6-alkyl or C3-C6-alkenyl;
v is 1 or 2;
in particular 2.
Particular preference is also given to compounds of the formula Ia where
R6 is hydroxyl, mercapto, phenylcarbonyloxy, C1-C6-alkylthio, phenylthio, Nxe2x80x94(C1-C6-alkoxy)-Nxe2x80x94(C1-C6-alkyl)amino, 1-tetrahydropyrrolyl or 2-tetrahydroisoxazolyl, where the phenyl radicals of the abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
in particular hydroxyl, phenylcarbonyloxy, C1-C4-alkylthio, phenylthio, Nxe2x80x94(C1-C4-alkoxy)-Nxe2x80x94(C1-C4-alkyl)amino, 1-tetrahydropyrrolyl or 2-tetrahydroisoxazolyl;
R7,R8,R9,R10,R11,R12 are hydrogen or C1-C4-alkyl, such as methyl or ethyl;
in particular hydrogen or methyl; or
R9 and R10 together with the carbon to which they are attached form a carbonyl group; or
R7 and R11 together form a xe2x80x94(CH2)xe2x80x94 or xe2x80x94(CH2)2xe2x80x94 chain.
Extraordinary preference is given to the compounds of the formula Ia where
R6 is hydroxyl, mercapto, phenylcarbonyloxy, C1-C6-alkylthio, phenylthio, where the phenyl radicals of the abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
in particular hydroxyl or phenylthio, where the phenyl radical may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy.
Preference is also given to compounds Ib, especially compounds Ib where the variables have the following meanings:
R20 is a radical as mentioned under R6;
R21 is hydrogen, C1-C6-alkyl or C1-C6-haloalkyl; in particular C1-C4-alkyl, such as methyl, ethyl, 1-methyleth-1-yl or 1,1-dimethyleth-1-yl, or C1-C4-haloalkyl, such as 2-fluoroethyl or 2,2,2-trifluoroethyl;
R22 is hydrogen, C1-C6-alkyl or C1-C6-haloalkyl, in particular hydrogen, C1-C4-alkyl, such as methyl or ethyl, or C1-C4-haloalkyl, such as trifluoromethyl; in particular hydrogen, methyl or trifluoromethyl.
Preference is also given to the compounds Ib where the variables have the following meanings:
R20 is hydroxyl, mercapto, halogen, OR13, SR13, SO2R14, OSO2R14, NR17R18, ONR18R19 or N-bonded heterocyclyl, where the heterocyclyl radical of the lastmentioned substituent may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R13 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkylaminocarbonyl, N,N-di-(C1-C6-alkyl) or C1-C6-alkylcarbonyl-C1-C6-alkyl, where the alkyl or cycloalkyl radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1 4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, hydroxycarbonyl, di-(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
is phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenylcarbonyl or heterocyclylcarbonyl, where the phenyl and the heterocyclyl radical of the 6 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R14 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-cycloalkyl, hydroxyl, C1-C6-alkoxy, di-(C1-C6-alkyl)amino or di-(C1-C6-haloalkyl)amino, where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
is phenyl, heterocyclyl, phenoxy or heterocyclyloxy, where the phenyl and the heterocyclyl radical of the lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R17 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-cycloalkyl, C1-C6-alkoxy or C3-C6-alkenyloxy, where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one to three radicals from the group below:
cyano, C1-C4-alkoxy or C1-C4-alkylthio;
is phenyl, heterocyclyl, phenyl-C1-C6-alkyl or heterocyclyl-C1-C6-alkyl, where the phenyl or heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R18, R19 are C1-C6-alkyl or C3-C6-alkenyl;
R21 is C1-C6-alkyl, such as methyl, ethyl, 1-methyleth-1-yl, or 1,1-dimethyleth-1-yl;
R22 is hydrogen or C1-C6-alkyl such as methyl or ethyl; in particular hydrogen or methyl.
Extraordinary preference is given to the compounds Ib where the variables have the following meaning:
R20 is hydroxyl.
Preference is also given to compounds of the formula Ic, especially compounds Ic where the variables have the following meanings:
R23 is C1-C6-alkyl or C3-C6-cycloalkyl; in particular cyclopropyl;
R24 is hydrogen.
Preference is also given to compounds of the formula Id, especially compounds Id where the variables have the following meanings:
R25 is C1-C6-alkyl or C3-C6-cycloalkyl.
Preference is furthermore given to the compounds I1 (xe2x89xa1I where Xxe2x95x90O, R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position) 
With respect to the variables R1 to R4 and Q, what is said above applies.
Particular preference is given to the compounds I1 where the variables have the following meanings:
R3 is nitro, cyano, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylsulfonyl or C1-C4-haloalkylsulfonyl;
R4 is halogen, such as chlorine or bromine, or C1-C4-alkyl, such as methyl or ethyl;
l is 0 or 1.
Furthermore, preference is also given to the compounds I2 (xe2x89xa1I where Xxe2x95x90O, R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position) 
With respect to the variables R1 to R4 and Q, what was said above applies.
Particular preference is given to the compounds I2 where the variables have the following meanings:
R3 is nitro, cyano, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfonyl or C1-C4-haloalkylsulfonyl;
R4 is halogen, such as chlorine or bromine, or C1-C4-alkyl, such as methyl or ethyl;
l is 0 or 1.
Preference is furthermore given to the compounds I, in particular the compounds Ia, Ib, I1 or I2, where the variables have the following meanings:
R1,R2 are hydrogen, hydroxyl, C1-C6-alkyl or C1-C6-alkoxy, where the alkyl radicals of the two lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkoxy, C1-C4-alkylsulfonyl or C1-C4-alkoxycarbonyl;
particularly preferably hydrogen, C1-C4-alkyl or C1-C4-alkoxy.
Preference is furthermore given to the compounds I1a (xe2x89xa1I where Xxe2x95x90O, R3 is attached in position 4, R4l is attached in position 5 and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in position 2 and Q=Q1).
Particular preference is given to the compounds I1a (xe2x89xa1I where Xxe2x95x90O, R3 is in position 4, R4l is in position 5 and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is in position 2), where the variables have the following meanings:
R1,R2 are C1-C4-alkyl or C1-C4-alkoxy;
in particular C1-C4-alkyl;
R3 is halogen;
l is 0;
R6 is hydroxyl;
R7,R8,R9,R10,R11,R12 are hydrogen or C1-C4-alkyl,
or R9 and R10 together with the carbon to which they are attached form a carbonyl group.
Preference is furthermore given to the compounds I2a (xe2x89xa1I where Xxe2x95x90O, R3 is attached in position 2, R4l is attached in position 5 and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in position 4 and Q=Q1).
Particular preference is given to the compounds I2a (xe2x89xa1I where Xxe2x95x90O, R3 is attached in position 2, R4l is attached in position 5 and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in position 4 and Q=Q1), where the variables have the following meanings:
R1,R2 are C1-C4-alkyl or C1-C4-alkoxy;
R3 is halogen;
l is 0;
R6 is hydroxyl or phenylthio, where the phenyl radical may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R7,R8,R9,R10,R11,R12 are hydrogen or C1-C4-alkyl; or R9 and R10 together with the carbon to which they are attached form a carbonyl group;
or R7 and R11 together form a xe2x80x94(CH2)xe2x80x94 or xe2x80x94(CH2)2xe2x80x94 chain, in particular a xe2x80x94(CH2)2xe2x80x94 chain.
Preference is furthermore given to the compounds I2b (xe2x89xa1I where Xxe2x95x90O, R3 is in position 2, R4l is in position 5 and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is in position 4).
Particular preference is given to the compounds I2b (xe2x89xa1I where Xxe2x95x90O, R3 is in position 2, R4l is in position 5 and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is in position 4), where the variables have the following meanings:
R1,R2 are C1-C4-alkyl or C1-C4-alkoxy; in particular C1-C4-alkoxy;
R3 is halogen;
l is 0;
R20 is hydroxyl;
R21 is C1-C4-alkyl;
R22 is hydrogen or C1-C4-alkyl; in particular hydrogen.
Extraordinary preference is given to the compounds I1a1 (xe2x89xa1I where Xxe2x95x90O, R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position, Q=Q1, R7 to R12=hydrogen), in particular to the compounds I1a1.n where the variables R1 to R4 and R6 are as defined in Table 1.
The given radical definitions X, R1 to R12, Q and l are preferred for the compounds according to the invention not only in combination with one another, but in each case also on their own.
where:
Het1 is 1-methoxy-N-methylamino;
Het2 is 1-tetrahydropyrrolyl;
Het3 is 1-tetrahydroisoxazolyl.
Extraordinary preference is also given to the compounds I1a2 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q1; R7, R8, R9, R11, R12=H and R10=CH3), in particular to the compounds I1a2.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1a3 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q1; R8, R9, R10, R11, R12=H and R7=CH3), in particular to the compounds I1a3.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1a4 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q1; R7, R8, R11, R12=H and R9, R10=CH3), in particular to the compounds I1a4.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1a5 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q1; R7, R8=CH3 and R9, R10, R11, R12=H), in particular to the compounds I1a5.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1a6 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q1; R7, R8, R9, R10=H and R11, R12=CH3), in particular to the compounds I1a6.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1a7 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q1; R7, R8, R11, R12=H and R9 and R10 together with the carbon to which they are attached form a carbonyl group), in particular to the compounds I1a7.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1a8 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q1; R7, R8, R11, R12=CH3 and R9 and R10 together with the carbon to which they are attached form a carbonyl group), in particular to the compounds I1a8.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1a9 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q1; R7 and R11 together form a xe2x80x94CH2xe2x80x94CH2xe2x80x94 chain and R8, R9, R10, R12=H), in particular to the compounds I1a9.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2a1 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q1; R7, R8, R9, R10, R11, R12=H), in particular to the compounds I2a1.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2a2 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q1; R7, R8, R9, R11, R12=H and R10=CH3), in particular to the compounds I2a2.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2a3 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q1; R8, R9, R10, R11, R12=H and R7=CH3), in particular to the compounds I2a3.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2a4 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q1; R7, R8, R11, R12=H and R9, R10=CH3), in particular to the compounds I2a4.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2a5 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q1; R7, R8=CH3, R9, R10, R11, R12=H), in particular to the compounds I2a5.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2a6 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q1; R7, R8, R9, R10=H and R11, R12=CH3), in particular to the compounds I2a6.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2a7 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q1; R7, R8, R11, R12=H and R9 and R10 together with the carbon to which they are attached form a carbonyl group), in particular to the compounds I2a7.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2a8 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q1; R7, R8, R11, R12=CH3 and R9 and R10 together with the carbon to which they are attached form a carbonyl group), in particular to the compounds I2a8.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2a9 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q1; R7 and R11 together form a xe2x80x94CH2xe2x80x94CH2xe2x80x94 chain and R8, R9, R10, R12=H), in particular to the compounds I2a9.n, where the variables R1 to R4 and R6 are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b1 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=CH3 and R22=H), in particular to the compounds I1b1.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b2 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=CH2CH3 and R22=H), in particular to the compounds I1b2.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b3 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=CH(CH3)2 and R22=H), in particular to the compounds I1b3.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b4 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=C(CH3)3 and R22=H), in particular to the compounds I1b4.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b5 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=CH2CF3 and R22=H), in particular to the compounds I1b5.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b6 (xe2x89xa1where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=CH3 and R22=CH3), in particular to the compounds I1b6.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b7 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R7xe2x80x9d is attached in the 2-position; Q=Q2; R21=CH2CH3 and R22=CH3), in particular to the compounds I1b7.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b8 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=CH(CH3)2 and R22=CH3), in particular to the compounds I1b8.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b9 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=C(CH3)3 and R22=CH3), in particular to the compounds I1b9.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b10 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=CH2CH3 and R22=CH3), in particular to the compounds I1b10.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b11 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=CH3 and R22=CH3), in particular to the compounds I1b11.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b12 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=CH2CH3 and R22=CF3), in particular to the compounds I1b12.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b13 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=CH(CH3)2 and R22=CF3), in particular to the compounds I1b13.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b14 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=C(CH3)3 and R22=CF3), in particular to the compounds I1b14.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b15 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q2; R21=CH2CF3 and R22=CF3), in particular to the compounds I1b15.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b1 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=CH3 and R22=H), in particular to the compounds I2b1.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b2 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=CH2CH3 and R22=H), in particular to the compounds I2b2.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b3 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=CH(CH3)2 and R22=H), in particular to the compounds I2b3.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b4 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=C(CH3)3 and R22=H), in particular to the compounds I2b4.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b5 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=CH2CF3 and R22=H), in particular to the compounds I2b5.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b6 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=CH3 and R22=CH3), in particular to the compounds I2b6.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b7 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R7xe2x80x9d is attached in the 24-position; Q=Q2; R21=CH2CH3 and R22=CH3), in particular to the compounds I2b7.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b8 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=CH(CH3)2 and R22=CH3), in particular to the compounds I2b8.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b9 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=C(CH3)3 and R22=CH3), in particular to the compounds I2b9.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b10 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=CH2CF3 and R22=CH3), in particular to the compounds I2b10.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b11 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=CH3 and R22=CF3), in particular to the compounds I2b11.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b12 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=CH2CH3 and R22=CF3), in particular to the compounds I2b12.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b13(xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=CH(CH3)2 and R22=CF3), in particular to the compounds I2b13.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1b14 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=C(CH3)3 and R22=CF3), in particular to the compounds I2b14.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I2b15 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q2; R21=CH2CF3 and R22=CF3), in particular to the compounds I2b15.n, where the variables R1 to R4 and R20 (which in this case corresponds to R6) are as defined in Table 1. 
Extraordinary preference is also given to the compounds I1c1 (xe2x89xa1I where X=O; R3 is attached in the 4-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q3; 1=0, R23=cyclopropyl and R24=H), in particular to the compounds Ic1.n, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I1c2 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d in the 2-position; Q=Q3; R4=CH3, R23=cyclopropyl and R24=H), in particular to the compounds I1c2.n, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I1c3 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d in the 2-position; Q=Q3; R4=Cl, R23=cyclopropyl and R24=H), in particular to the compounds I1c3.n, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I1c4 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d in the 2-position; Q=Q3; R4=Br, R23=cyclopropyl and R24=H), in particular to the compounds I1c4, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I2cl (xe2x89xa1I where X=O; R3 is attached in the 2-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q3; 1=0; R23=cyclopropyl and R24=H), in particular to the compounds I2c1.n, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I2c2 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d in the 4-position; Q=Q3; R4=CH3, R23=cyclopropyl and R24=H), in particular to the compounds I2c2.n, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I2c3 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d in the 2-position; Q=Q3; R4=Cl, R23=cyclopropyl and R24=H), in particular to the compounds I2c3.n, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I2c4 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d in the 4-position; Q=Q3; R4=Br, R23=cyclopropyl and R24=H), in particular to the compounds I2c4, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I1d1 (xe2x89xa1I where X=O; R3 is attached in the 4-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q4; 1=0; R25=cyclopropyl), in particular to the compounds I1d1.n, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I1d2 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q4; R4=CH3, R25=cyclopropyl), in particular to the compounds I1d2.n, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I1d3 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q4; R4=Cl, R25=cyclopropyl), in particular to the compounds I1d3.n, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I1d4 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q4; R4=Br, R25=cyclopropyl), in particular to the compounds I1d4, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I2d1 (xe2x89xa1I where X=O; R3 is attached in the 2-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 4-position; Q=Q4; 1=0; R25=cyclopropyl), in particular to the compounds I2d1.n, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I2d2 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q4; R4=CH3, R25=cyclopropyl), in particular to the compounds I2a2.n, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I2d3 (xe2x89xa1I where X=O; R3 is attached in the 2-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q4; R4=Cl, R25=cyclopropyl), in particular to the compounds I2d3.n, where the variables R1 to R3 are as defined in Table 2. 
Extraordinary preference is also given to the compounds I2d4 (xe2x89xa1I where X=O; R3 is attached in the 4-position, R4 is attached in the 5-position and xe2x80x9cP(xe2x95x90X)R1R2xe2x80x9d is attached in the 2-position; Q=Q4; R4=Br, R25=cyclopropyl), in particular to the compounds I2d4, where the variables R1 to R3 are as defined in Table 2. 
The phosphorus-containing benzoyl derivatives of the formula I can be obtained by different routes, for example by the following processes:
A. Preparation of compounds of the formula Ia where R6=halogen by reaction of compounds of the formula Ia (xe2x89xa1I where Q=Q1) where R6=hydroxyl with halogenating agents: 
Suitable halogenating agents are, for example, phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N,N-dimethylammonium chloride, oxalyl bromide, phosphorus oxybromide, etc.
The starting materials are generally employed in equimolar amounts. However, it may also be advantageous to employ an excess of one or the other component.
Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or mixtures of these. However, it is also possible to carry out the reaction without a solvent.
In general, the reaction temperature is in the range from 0xc2x0 C. to the boiling point of the reaction mixture.
Work-up can be carried out in a manner known per se to afford the product.
B. Preparation of compounds of the formula Ia (xe2x89xa1I where Q=Q1) where R6=OR13, OSO2R14, OPR15R16, OPOR15R16 or OPSR15R16 by reaction of compounds of the formula Ia (xe2x89xa1I where Q=Q1) where R6=hydroxyl with alkylating, sulfonylating or phosphonylating agents IIxcex1, IIxcex2, IIxcex3, IIxcex4 or IIxcex5. 
L1 is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, hetaryl, for example imidazolyl, carboxylate, for example acetate, or sulfonate, for example mesylate or triflate, etc.
The compounds of the formula IIxcex1, IIxcex2, IIxcex3, IIxcex4 or IIxcex5 can be employed directly, such as in the case of the carbonyl halides, or generated in situ, for example activated carboxylic acids (using carboxylic acid and dicyclohexylcarbodiimide, etc.).
The starting materials are generally employed in equimolar amounts. However, it may also be advantageous to employ an excess of one or the other component.
If appropriate, it may also be advantageous to carry out the reaction in the presence of a base. The reactants and the base are advantageously employed in equimolar amounts. In certain cases, an excess of base of, for example, 1.5 to 3 molar equivalents may be advantageous.
Suitable bases are tertiary alkylamines, such as triethylamine, aromatic amines, such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal bicarbonates, such as sodium bicarbonate and potassium bicarbonate, alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, or alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine or pyridine.
Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.
The reaction temperature is generally in the range from 0xc2x0 C. to the boiling point of the reaction mixture.
Work-up can be carried out in a manner known per se to afford the product.
C. Preparation of compounds of the formula Ia (xe2x89xa1I where Q=Q1) where R6=OR13, SR13, POR15R16, NR17R18, ONR18R19, N-bonded heterocyclyl or O-(N-bonded heterocyclyl) by reaction of compounds of the formula Ia (xe2x89xa1I where Q=Q1) where R6=halogen, OSO2R14 with compounds of the formula IIIxcex1, IIIxcex2, IIIxcex3, IIIxcex4, IIIxcex5, IIIxcex7 or III"THgr", if appropriate in the presence of a base or with prior salt formation. 
The starting materials are employed in equimolar amounts. However, it may also be advantageous to employ an excess of one or the other component.
If appropriate, it may also be advantageous to carry out the reaction in the presence of a base. The reactants and the base are advantageously employed in equimolar amounts. An excess of base of, for example, from 1.5 to 3 molar equivalents, based on Ia (xe2x89xa1I where Q=Q1) where R6=halogen, OSO2R14, may be advantageous in certain cases.
Suitable bases are tertiary alkylamines, such as triethylamine, aromatic amines, such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal bicarbonates, such as sodium bicarbonate and potassium bicarbonate, alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, or alkali metal hydrides, for example sodium hydride. Preference is given to using sodium hydride or potassium tert-butoxide.
Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or mixtures of these.
In general, the reaction temperature is in the range from 0xc2x0 C. to the boiling point of the reaction mixture.
Work-up can be carried out in a manner known per se to afford the product.
D. Preparation of compounds of the formula Ia (xe2x89xa1I where Q=Q1) where R6=SOR14, SO2R14 by reaction of compounds of the formula Ia (xe2x89xa1I where Q=Q1) where R6=SR14 with an oxidizing agent. 
Suitable oxidizing agents are, for example, m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst, such as tungstate.
The starting materials are generally employed in equimolar amounts. However, it may also be advantageous to employ an excess of one or the other component.
Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile or dimethylformamide, or esters, such as ethyl acetate, or mixtures of these.
In general, the reaction temperature is in the range from 0xc2x0 C. to the boiling point of the reaction mixture.
Work-up can be carried out in a manner known per se to afford the product.
E. Preparation of compounds of the formula Ia (xe2x89xa1I where Q=Q1) where R6=OH by reaction of an activated phosphorus-containing benzoic acid of the formula IVxcex1 or a phosphorus-containing benzoic acid IVxcex2, which is preferably activated in situ, with a cyclohexanedione of the formula V to give the acylation product, followed by rearrangement. 
L2 is a nucleophilically replaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, etc.
The activated benzoic acid IV can be employed directly, such as in the case of the benzoyl halides, or generated in situ, for example using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic acid ester, 2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole, etc.
If appropriate, it may be advantageous to carry out the acylation reaction in the presence of a base. The reactants and the auxiliary base are advantageously employed in equimolar amounts. A slight excess of auxiliary base, for example from 1. to 1.5 molar equivalents, based on IVxcex1 or IVxcex2, may be advantageous in certain cases.
Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.
If the activated carboxylic acid component used is a phosphorus-containing benzoyl halide, it may be advantageous to cool the reaction mixture to 0-10xc2x0 C. when adding this reaction partner. The mixture is subsequently stirred at 20-100xc2x0 C., preferably at 25-50xc2x0 C., until the reaction has gone to completion. Work-up is carried out in a customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents which are suitable for this purpose are, in particular, methylene chloride, diethyl ether and ethyl acetate. The organic phase is dried and the solvent is removed, and the crude ester can then be employed for the rearrangement without further purification.
The rearrangement of the esters VI to the compounds of the formula Ia is advantageously carried out at 20-100xc2x0 C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as catalyst.
Suitable solvents are, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.
Suitable bases are tertiary amines, such as triethylamine, aromatic amines, such as pyridine, or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably employed in equimolar amounts or in up to four-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonate, preferably in twice the equimolar amount, based on the ester.
Suitable cyano compounds are inorganic cyanides, such as sodium cyanide or potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin or trimethylsilyl cyanide. They are employed in an amount of from 1 to 50 mol percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilyl cyanide, for example in an amount of from 5 to 15, preferably 10, mol percent, based on the ester.
Work-up can be carried out in a manner known per se. The reaction mixture is, for example, acidified with dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract can be extracted with 5-10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the resulting precipitate is filtered off with suction and/or the mixture is extracted with methylene chloride or ethyl acetate and the extract is dried and concentrated.
F. Preparation of compounds of the formula Ib (xe2x89xa1I where Q=Q2) where R20=halogen by reaction of compounds of the formula Ib (xe2x89xa1I where Q=Q2) where R20=hydroxyl with halogenating agents: 
What has been said in section A applies analogously.
G. Preparation of compounds of the formula Ib (xe2x89xa1I where Q=Q2) where R20=OR13, OSO2R14, OPR15R16, OPOR15R16 or OPSR15R16 by reaction of compounds of the formula Ib (xe2x89xa1I where Q=Q2) where R6=hydroxyl with alkylating, sulfonylating or phosphonylating agents IIxcex1, IIxcex2, IIxcex3, IIxcex4 or IIxcex5. 
What has been said in section B applies analogously.
H. Preparation of compounds of the formula Ib (xe2x89xa1I where Q=Q2) where R6=OR13, SR13, POR15R16, NR17R18, ONR18R19, N-bonded heterocyclyl or Oxe2x80x94(N-bonded heterocyclyl) by reaction of compounds of the formula Ib (xe2x89xa1I where Q=Q2) where R20=halogen, OSO2R14 with compounds of the formula IIIxcex1, IIIxcex2, IIIxcex3, IIIxcex4, IIIxcex5, IIIxcex7 or III"THgr", if appropriate in the presence of a base or with prior salt formation. 
What has been said in section C applies analogously.
I. Preparation of compounds of the formula Ib (xe2x89xa1I where Q=Q2) where R20=SOR14, SO2R14 by reaction of compounds of the formula Ib (xe2x89xa1I where Q=Q2) where R20=SR14 with an oxidizing agent. 
What has been said in section D applies analogously.
K. Preparation of compounds of the formula Ib (xe2x89xa1I where Q=Q2) where R20xe2x89xa0hydroxyl by reaction of a metallated pyrazole derivative of the formula VII with a phosphorus-containing benzoic acid derivative of the formula VIxcex3: 
M is a metal, in particular an alkali metal, such as lithium or sodium, an alkaline earth metal, such as magnesium, or a transition metal, such as palladium, nickel, etc., and L3 is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, alkylsulfonate, such as mesylate, haloalkylsulfonate, such as triflate, or cyanide.
The reaction is generally carried out at temperatures from xe2x88x92100xc2x0 C. to the reflux temperature of the reaction mixture. Suitable solvents are inert aprotic solvents, such as ethers, such as diethyl ether, tetrahydrofuran. The compounds of the formula Ivxcex3 are generally employed in excess; however, it may also be advantageous to employ them in equimolar amounts or substoichiometric amounts. Work-up is carried out to afford the product.
The metallated pyrazole derivatives of the formula VII can be generated in a manner known per se by reacting pyrazoles halogenated in the 4-position with metals such as lithium, sodium, magnesium etc., or with organometallic compounds, for example butyllithium. However, it is also possible to metallate pyrazoles which are linked to hydrogen in the 4-position directly, for example using the abovementioned metals or organometallic compounds. The reactions are generally carried out in an inert aprotic solvent, preferably in ether, such as diethyl ether, tetrahydrofuran, etc. The reaction temperature is in the range from xe2x88x92100xc2x0 C. to the boiling point of the reaction mixture. The compounds of the formula VII are generally directly reacted further or generated in situ.
L. Preparation of compounds of the formula Ib (xe2x89xa1I where Q=Q2) where R20=hydroxyl by reaction of an activated phosphorus-containing benzoic acid of the formula IVxcex1 or a phosphorus-containing benzoic acid IVxcex2, which is preferably activated in situ, with a pyrazole of the formula VIII to give the acylating product, followed by rearrangement. 
What has been said in section E applies analogously.
However, it is also possible to generate the ester IX in situ by reacting a pyrazole of the formula VIII, or an alkali metal salt thereof, with a phosphorus-containing benzene derivative of the formula X in the presence of carbon monoxide, a catalyst and a base. 
L4 is a leaving group, such as halogen, for example chlorine, bromine or iodine, or sulfonate, such as mesylate or triflate; preference is given to bromine or triflate.
If appropriate, the ester IX reacts directly to give the phosphorus-containing benzoyl derivative of the formula Ib.
Suitable catalysts are palladium-ligand complexes in which the palladium is present in oxidation state 0, metallic palladium, which has optionally been absorbed on a carrier, and preferably palladium(II) salts. The reaction with palladium(II) salts and metallic palladium is preferably carried out in the presence of complex ligands.
An example of a suitable palladium(0)-ligand complex is tetrakis(triphenylphosphine)palladium.
Metallic palladium is preferably absorbed on an inert carrier such as, for example, active carbon, silica, alumina, barium sulfate or calcium carbonate. The reaction is preferably carried out in the presence of complex ligands such as, for example, triphenylphosphine.
Examples of suitable palladium(II) salts are palladium acetate and palladium chloride. The presence of complex ligands such as, for example, triphenylphosphine is preferred.
Suitable complex ligands for the palladium-ligand complexes, or in whose presence the reaction is preferably carried out with metallic palladium or palladium(II) salts, are tertiary phosphines whose structure is represented by the following formulae: 
where z is from 1 to 4 and the radicals Ra to Rg are C1-C6-alkyl, aryl-C1-C2-alkyl or preferably aryl. Aryl is, for example, naphthyl and unsubstituted or substituted phenyl, such as, for example, 2-tolyl and, in particular, unsubstituted phenyl.
The complex palladium salts can be prepared in a manner known per se starting from commercially obtainable palladium salts such as palladium chloride or palladium acetate and the appropriate phosphines, such as, for example, triphenylphosphine or 1,2-bis(diphenylphosphino)ethane. Many of the complex palladium salts are commercially available. Preferred palladium salts are [(R)(+)-2,2xe2x80x2-bis(diphenylphosphino)-1,1xe2x80x2-binaphthyl]palladium(II) chloride, bis(triphenylphosphine)palladium(II) acetate and, in particular, bis(triphenylphosphine)palladium(II) chloride.
The palladium catalyst is generally employed in a concentration of from 0.05 to 5 mol %, and preferably 1-3 mol %.
Suitable bases are tertiary amines, such as, for example, N-methylpiperidine, ethyldiisopropylamine, 1,8-bisdimethylaminonaphthalene or, in particular, triethylamine. Also suitable are alkali metal carbonates, such as sodium carbonate or potassium carbonate. However, mixtures of potassium carbonate and triethylamine are also suitable.
In general, from 2 to 4 molar equivalents, in particular 2 molar equivalents, of the alkali metal carbonate and from 1 to 4 molar equivalents, in particular 2 molar equivalents, of the tertiary amine are employed, based on the phosphorus-containing benzene derivative of the formula X.
Suitable solvents are nitrites, such as benzonitrile and acetonitrile, amides, such as dimethylformamide, dimethylacetamide, tetra-C1-C4-alkylureas or N-methylpyrrolidone and, preferably, ethers such as tetrahydrofuran, methyl tert-butyl ether. Particularly preferred solvents are ethers such as 1,4-dioxane and dimethoxyethane.
M. Preparation of compounds of the formula Ic (xe2x89xa1I where Q=Q3) where R24=H by reaction of a 1,3-dicarbonyl compound of the formula XI with hydroxylamine. 
L5 is an Oxe2x80x94C1-C6-alkyl or N(C1-C6-alkyl)2 group. The 1,3-dicarbonyl compound of the formula XI is reacted with hydroxylamine which is generated in situ, for example from hydroxylamine salt using a base or an acid acceptor, such as triethylamine or sodium acetate.
The starting material of the formula XI is obtained by reacting the xcex2-keto esters of the formula XII, which are known per se, with an activated phosphorus-containing benzoic acid IVxcex1. The acylation product XIII is subsequently converted into the 1,3-diketone XIV using, for example, p-toluenesulfonic acid as catalyst in an inert solvent, such as toluene. The 1,3-diketone XIV is subsequently reacted with an orthoester or dimethylformamide dialkyl acetal to give the 1,3-dicarbonyl compound of the formula XI. 
N. Preparation of compounds of the formula Ic (xe2x89xa1I where Q=Q3) by cycloaddition of the xcex1,xcex2-unsaturated benzoyl derivative XV with a nitrile oxide of the formula XVI 
The xcex1,xcex2-unsaturated benzoyl derivative XV is obtained by ethynylation of the activated phosphorus-containing benzoic acid of the formula IVxcex1. 
Z is a metal such as lithium, an organotin radical such as Sn(C4H9)3 or a zinc radical such as ZnCl or ZnBr.
O. Preparation of compounds of the formula Id (xe2x89xa1I where Q=Q4) by reaction of the cyanoketone XVII with an activated phosphorus-containing benzoic acid of the formula IVxcex1 in the presence of a base such as triethylamine, sodium carbonate, sodium hydride or magnesium ethoxide in an inert organic solvent such as diethyl ether, tetrahydrofuran, N,N-diethylformamide, dichloromethane or acetonitrile. 
The phosphorus-containing benzoyl halides of the formula IVxcex1 where L2=halogen can be prepared in a manner known per se by reacting the benzoic acids of the formula IVxcex2 with halogenating agents such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride, oxalyl bromide.
The phosphorus-containing benzoic acids of the formula IVxcex2 can be prepared in a manner known per se by acidic or basic hydrolysis from the corresponding phosphorus-containing benzoic esters IVxcex4 (cf. J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 4th edition, Wiley, New York, p. 378 ff.) 
where T is C1-C6-alkoxy.
The phosphorus-containing benzoic esters IVxcex4 are obtainable by different routes:
They can be obtained by electrophilic or nucleophilic aromatic substitution of benzoic esters of the formula XVIII and, if appropriate, further functionalization of the group thus introduced. 
For example, the ester of the formula XVIII can be nitrated analogously to known methods (R3=NO2; cf. J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 4th edition, p. 522 ff.), brominated or chlorinated (R3=Cl, Br; cf. J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 4th edition, p. 531 ff.).
The abovementioned electrophilic aromatic substitution reaction may result in mixtures of isomers, which can be separated or purified by distillation, crystallization or chromatographic methods.
Phosphorus-containing benzoic esters of the formula IVxcex4 where R3=NH2 can be obtained by reduction of the corresponding nitro compounds of the formula IVxcex4 where R3=NO2. 
Suitable reducing agents are, inter alia, metals such as iron or zinc in the presence of hydrochloric acid and catalytically activated hydrogen (cf. J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 4th edition, p. 1216 ff.)
Phosphorus-containing benzoic esters of the formula IVxcex4 where R3=(C1-C6-alkylsulfonyl)amino, (C1-C6-haloalkylsulfonyl)amino can be obtained by reaction of the corresponding amino compounds with appropriately substituted sulfonyl chlorides in the presence of a base (cf.
T. W. Green et al., xe2x80x9cProtective Groups in Organic Synthesisxe2x80x9d, p. 379 f.) 
The latter can be converted into the corresponding N-alkyl derivatives by alkylation in the presence of a base. 
Suitable bases are, inter alia, sodium hydride, potassium hydride, potassium tert-butoxide, and suitable alkyl halides are alkyl bromides and alkyl iodides (cf. J. P. Dunn et al., J. Med. Chem. 1981, 24, p. 1097).
Phosphorus-containing benzoic esters of the formula IVxcex4 where R3=halogen, cyano, C1-C6-alkyl, C1-C6-alkylthio or C1-C6-haloalkylthio can be obtained from the corresponding amino compounds by Sandmeyer reaction or related reactions (cf. J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 4th edition, pp. 723-724, pp. 669-671) 
If appropriate, it may be advantageous to carry out the reactions in the presence of metal catalysts such as, for example, copper(I) or palladium(II) (cf., for example, Kikukawa et al., J. Org. Chem. 1983, 48, 1333).
Phosphorus-containing benzoic esters of the formula IVxcex4 where R3=S(O)1,2xe2x80x94C1-C6-alkyl or S(O)1,2xe2x80x94C1-C6-haloalkyl can be obtained by reaction of the corresponding sulfur compounds with an oxidizing agent such as bromine, peroxyacetic acid, m-chloroperbenzoic acid and hydrogen peroxide, if appropriate in the presence of a catalyst such as tungstate. 
Phosphorus-containing benzoic esters of the formula IVxcex4 here R3=aminosulfonyl, C1-C6-alkylaminosulfonyl or di(C1-C6-alkyl)aminosulfonyl can be obtained by reaction of the corresponding sulfonyl chloride with ammonia or suitable amines. If appropriate, it may be useful to operate in the presence of a base such as triethylamine, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate or pyridine (cf. J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 4th edition, p. 499). The sulfonyl chloride is obtained by sulfochlorination of the corresponding diazonium salt. 
Phosphorus-containing benzoic esters of the formula IVxcex4 where R3=C1-C6-alkoxy or C1-C6-haloalkoxy can be obtained by alkylation of the corresponding phenols in the presence of a base. Suitable bases are, in addition to the customary bases, in particular sodium carbonate, potassium carbonate, sodium hydride or potassium tert-butoxide. Preferred alkylating agents are appropriate halogenated or non-halogenated alkyl bromides or chlorides (cf., for example, H. Fener et al., xe2x80x9cThe Chemistry of the Ether Linkagexe2x80x9d, Wiley, New York, 1967, pp. 445-498.)
The phenols can be obtained by boiling down of corresponding diazonium compounds. 
Phosphorus-containing benzoic esters of the formula IVxcex4 where R3=PXR1R2 can be obtained by reaction of compounds of the formula IVxcex4 where R3=Br, I, OSO2CF3 etc., with suitable phosphonous acids or phosphorous acids in the presence of a transition metal catalyst such as nickel or palladium and, if appropriate, of a base (cf., for example, T. Hirao et al., Synthesis 1981, 56). 
Phosphorus-containing benzoic esters of the formula IVxcex4 where R3=phenyl can be prepared by reaction of a corresponding bromide or iodide of the formula IVxcex4 where R3=Br or I with a phenyl bromide or phenyl iodide, which may be substituted, in the presence of copper (cf. Ranta et al., Synthesis 1974, 9; Goshaer et al., Russ. Chem. Rev. 1972, 41, 1046) 
Phosphorus-containing benzoic esters of the formula IVxcex4 where R3=unsub. or sub. phenyl, unsub. or sub. heterocyclyl can be obtained by reaction of compounds of the formula IVxcex4 where R3=a leaving group such as bromine, iodine, triflate, fluorosulfonyloxy, etc., with an unsub. or sub. phenyl or heterocyclyl stannane (Stille coupling), an unsub. or sub. phenyl or heterocyclyl boron compound (Suzuki coupling) or an unsub. or sub. phenyl or heterocyclyl zinc compound (Negishi coupling) in a manner known per se (cf. Tetrahedron Lett. 1986, 27, 5265) in the presence of a palladium or nickel catalyst and, if appropriate, a base. 
Arxe2x80x2=unsub. or sub. phenyl or heterocyclyl
Met=Sn(C1-C4-alkyl)3, B(OH)2, ZnBr, ZnCl
Phosphorus-containing benzoic esters of the formula IVxcex4 where R3=unsub. or sub. heterocyclyl can also be obtained by constructing the heterocycle from suitable precursors.
1,2,4-Oxadiazoline derivatives, for example, can be prepared from aldoximes of the formula XIX by condensation with aldehydes of the ketones (cf., for example, Arch. Pharm. 1993, 326, 383-389).
The thioamides of the formula XX are suitable precursors for 2-thiazolinyl derivatives (cf., for example, Tetrahedron 1986, 42, 1449-1460) and for 2-thiazolyl derivatives (cf., for example, Houben-Weyl, xe2x80x9cMethoden der organischen Chemiexe2x80x9d[Methods of Organic Chemistry], 4th edition, Vol. E5, p. 1268 ff. (1985)).
2-Oxazolinyl, 2-thiazolinyl and 2-imidazolinyl derivatives are obtainable from the carboxylic acids of the formula XXI (cf., for example, Tetrahedron Lett. 1981, 22, 4471-4474).
According to processes known from the literature, it is possible to prepare 1,3-thiazole-5(4H)-thion-2-yl or 5-oxo-2-imidazolin-2-yl derivatives from carbonyl halides of the formula XXII where Hal is halogen, in particular from carbonyl chlorides (cf., for example, Helv. Chim. Acta, 1986, 69, 374-388; Heterocycles 1989, 29, 1185-1189).
Furthermore, it is possible to prepare 2-oxazolyl derivatives from the carboxylic acids of the formula XXI or the carbonyl halides of the formula XXII (cf., for example, Heterocyclic Chem. 1991, 28, 17-28).
The conversion of oximes of the formula XXIV into 4,5-dihydroisoxazol-3-yl or isoxazol-3-yl derivatives can be carried out in a manner known per se via the intermediate of the hydroxamoyl chlorides or bromides. Using the latter, nitrile oxides are generated in situ which react with alkenes or alkynes to give the desired products (cf., for example, Chem. Ber. 1973, 106, 3258-3274). 1,3-Dipolar cycloaddition with chlorosulfonyl isocyanate to the nitrile oxide formed in situ affords 1,2,4-oxadiazolin-5-on-3-yl derivatives (cf., for example, Heterocycles 1988, 27, 683-685).
The aldehydes of the formula XXV can be converted into 2,4-dihydro-1,2,4-triazol-3-on-5-yl derivatives via the intermediate of the semicarbazones (cf., for example, J. Heterocyclic Chem. 1986, 23, 881-883).
2-Imidazolinyl derivatives are preparable from benzonitriles of the formula XXVI by known methods (cf., for example, J. Org. Chem. 1987, 52, 1017-1021).
It is also possible to prepare 1,2,4-triazol-3-yl derivatives by known processes from the benzonitriles of the formula XXVI (cf., for example, J. Chem. Soc. 1954, 3461-3464).
The aldehydes XXV can be reacted in a manner known per se by Wittig reaction with phosphonium salts (Ph)3P+CH2COR*Xxe2x88x92 (J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd edition, p. 864 ff., Wiley-Interscience Publication, 1985) to give xcex1,xcex2-unsaturated ketones XXVII. By reaction with hydroxylamine, these give the corresponding oximes which can be converted into the 5-isoxazolyl derivatives by oxidative cyclization (J. Am. Chem. Soc. 1972, 94, 9128) (the meaning of R* thus corresponds to the meaning of a radical by which the heterocyclyl may be substituted).
It is also possible to convert the aldehydes XXV with alkoxymethylphosphonium salts in a manner known per se (J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd edition, p. 864 ff., Wiley-Interscience Publication, 1985) into the corresponding enol ethers. Cleavage of these enol ethers analogously to processes known from the literature yield the acetaldehyde derivatives XXVIII. By bromination in the xcex1-position these can be converted into the xcex1-bromoacetaldehyde derivatives (Tetrahedron Lett. 1988, 29, 5893), which afford, by cyclization with amides, thioamides and amidines, oxazoles, thiazoles and imidazoles. Furthermore, the acetaldehyde derivatives XXVIII can be converted with dimethylformamide dimethyl acetal into corresponding enamines which can then be converted into isoxazoles or pyrazoles using hydroxylamines and hydrazines, respectively.
Furthermore, the aldehydes XXV can be converted into hydroxyketone derivatives by Aldol reaction with ketones. Subsequent oxidation leads to 1,3-diketones which can be converted into isoxazoles, pyrazoles or pyrimidines using hydroxylamine, hydrazines or amidines.
The aldehydes XXV can also be converted by methods known from the literature (Houben-Weyl, xe2x80x9cMethoden der organischen Chemiexe2x80x9d[Methods of Organic Chemistry], 4th edition, Vol. E14b) into the corresponding diazo compounds XXIX. 1,3-dipolar cycloaddition to alkenes or alkynes and subsequent isomerization leads to pyrazolines or pyrazoles.
The aldehyde XXV can be prepared analogously to processes known from the literature, for example from the corresponding methyl compound XXX, by bromination, for example with N-bromosuccinimide or 1,3-dibromo-5,5-dimethylhydantoin, and subsequent oxidation (cf. Synth. Commun. 1992, 22, 1967-1971).
The oximes of the formula XXIV are advantageously obtained by reacting, in a manner known per se, aldehydes of the formula XXV with hydroxylamine (cf. J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd edition, pp. 805-806, Wiley, New York, 1985).
The conversion of the oximes XXIV into the nitrites XXVI can also be carried out by processes known per se (cf. J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd edition, pp. 931-932, Wiley, New York, 1985).
The nitrites of the formula XXVI can be converted in a manner known per se with hydroxylamine into the corresponding aldoximes XIX, converted with hydrogen sulfide into the thioamides XX or hydrolyzed to give the carboxylic acids XXI. The latter can also be obtained from the aldehydes XXV by oxidation (cf. J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd edition, p. 629 ff., Wiley, New York, 1985).
The acyl halides XXII can be obtained analogously to standard processes from the corresponding carboxylic acids of the formula XXI. 
The phosphorus-containing compounds of the formula IVxcex4 are obtainable by reaction of compounds of the formula XXXII where L5=bromine, iodine, triflate and a corresponding substituted phosphorous acid or phosphonous acid in the presence of a transition metal catalyst, such as nickel or palladium, and, if appropriate, a base (cf., for example, T. Hirao et al., Synthesis 1981, 56.) 
The compounds of the formula XXXII where L5=Br, I are obtained from the corresponding nitro compounds by reaction of the nitro group and subsequent Sandmeyer reaction. The compounds of the formula XXXII where L5=OSO2CF3 can be obtained by reacting the corresponding phenol with trifluoromethylsulfonyl chloride or trifluoromethylsulfonic anhydride.
The compounds of the formula IVxcex4 where R1, R2=C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylamino etc., can also be obtained by reaction of nucleophilically substitutable phosphorus compounds of the formula IVxcex4 where Lxe2x80x2, Lxe2x80x3=a leaving group, such as halogen, C1-C6-alkoxy, etc., with suitable alcohols, amines or mercaptans, if appropriate in the presence of a base, (cf., for example, L. J. Kaplan, J.Org. Chem. 1979, 44, 2226; Houben-Weyl, xe2x80x9cMethoden der organischen Chemiexe2x80x9d[Methods of Organic Chemistry], Vol. XII/1, p. 423 ff.; R. Z. Greenley et al., J. Org. Chem. 1964, 29, 1009). 
Compounds of the formula IVxcex4 where Lxe2x80x2, Lxe2x80x3=halogen can be obtained by reaction of compounds of the formula IVxcex4 where R1, R2=OCH3 with halogenating agents (cf. z. B. W. Althoff et al., Chem. Ber. 1978, 111, 1845).
Suitable halogenating agents are, inter alia, phosgene, thionyl chloride and thionyl bromide.
Compounds of the formula IVxcex2 are furthermore obtainable by oxidation of compounds of the formula XXXIII. 
Suitable oxidizing agents are, for example, potassium permanganate (cf., for example, Houben Weyl, xe2x80x9cMethoden der Organischen Chemiexe2x80x9d[Methods of Organic Chemistry], Vol. IV/1a, 1981, and Vol. VIII, 1952; E. I. Bengtsson, Acta Chem. Scand. 1953, 7, 774), chromium(VI) compounds (cf., for example, A. W. Singer et al., Org. Synth. Coll. Vol. III 1955, 740) or atmospheric oxygen in the presence of a catalyst such as, for example, cobalt or manganese (cf., for example, A. S. Hay et al., Can. J. Chem. 1965, 43, 1306).
The compounds of the formula XXXIII are obtainable by reaction of organometallic compounds of the formula XXXIV (where Metxe2x80x2=Li, Mg) with phosphorus compounds carrying nucleophilically replaceable groups (L=halogen, such as Cl, Br, alkoxy, etc.) (cf., for example, A. Berger et al., J. Org. Chem. 1951, 16, 1250; M. Sander, Chem. Ber. 1960, 93, 1220). 
These compounds can also be obtained by oxidation of the corresponding phosphorus(III) compounds, which can be prepared analogously to the reaction shown above. 
Suitable oxidizing agents are, for example, hydrogen peroxide, peroxyacetic acid, etc.
The compounds of the formula XXXIII (where R2=C1-C6-alkoxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, etc.) can furthermore be obtained by reacting a phosphorus compound of the formula XXXV with an alkyl halide (Arbuzov reaction). 
Preferred alkyl halides are the corresponding bromides and iodides (cf., for example, B. A. Arbuzov, Pure Appl. Chem. 1964, 9, 307; G. M. Kosolapoff, Org. React. 1951, 6, 273). 
In general, it is possible to introduce or synthesize the radical R3 at a suitable stage of the reaction sequence of the preparation of compounds of the formula I, where these reactions are described above or can be prepared analogously to known processes.
It may also be feasible to change the order of the reaction steps.
Furthermore, it is possible to modify the substituents R1 and R2 at a suitable stage of the reaction sequence. For example, the radicals R1, R2=C1-C6-alkoxy can be converted by reaction with organometallic compounds into R1, R2=C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl etc. Organometallic reagents which are suitable for this purpose are appropriate organolithium or organomagnesium compounds (cf., for example, Houben-Weyl, xe2x80x9cMethoden der Organischen Chemiexe2x80x9d[Methods of Organic Chemistry], Vol. E. 2, p. 38 ff., Wiley, New York).
Novel are the phosphorus-containing benzoic acid derivatives of the formula IV 
where:
X is oxygen or sulfur;
R1,R2 are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, mercapto, C1-C6-alkylthio, C3-C6-alkenylthio, C3-C6-alkynylthio, amino, C1-C6-alkylamino, di(C1-C6-alkyl)amino, (C1-C6-alkoxy)(C1-C6-alkyl)amino, (C3-C6-alkenyl)(C1-C6-alkyl)amino, (C3-C6-alkynyl)(C1-C6-alkyl)amino, di(C3-C6-alkenyl)amino or di(C3-C6-alkynyl)amino, where the abovementioned alkyl, alkenyl or alkynyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, di(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl,
are phenyl or heterocyclyl, where the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
are phenoxy which may by partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl; or
R1 and R2 together form a xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94NR5xe2x80x94(CH2)mxe2x80x94NR5xe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94NR5xe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94NR5xe2x80x94, xe2x80x94(CH2)nxe2x80x94Oxe2x80x94, xe2x80x94(CH2)nxe2x80x94Sxe2x80x94 or xe2x80x94(CH2)nxe2x80x94NR5 chain which may carry one to three radicals from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, Cl-C4-alkoxy, C1-C4-alkoxycarbonyl or phenyl which is unsubstituted or partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl; or
R1 and R2 together form xe2x80x94(CH2)p chain which may be interrupted by oxygen, sulfur or NR5 and/or may carry one to three radicals from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or phenyl which is unsubstituted or partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R3 is cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, aminosulfonyl, C1-C6-alkylaminosulfonyl, di(C1-C6-alkyl)aminosulfonyl, (C1-C6-alkylsulfonyl)amino, (C1-C6-haloalkylsulfonyl)amino, Nxe2x80x94(C1-C6-alkyl)xe2x80x94Nxe2x80x94(C1-C6-alkylsulfonyl)amino, Nxe2x80x94(C1-C6-alkyl)xe2x80x94Nxe2x80x94(C1-C6-haloalkylsulfonyl)amino, xe2x80x94P(xe2x95x90X)R1R2, phenyl or heterocyclyl, where the two last-mentioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R4 is nitro, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl or C1-C6-alkylsulfonyl;
R5 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy;
l is 0, 1 or 2;
m is 2, 3 or 4;
n is 3, 4 or 5;
p is 4, 5 or 6;
R26 is a radical which can be removed by hydrolysis.
Examples of radicals which can be removed by hydrolysis are alkoxy, phenoxy, alkylthio and phenylthio radicals, which may be unsubstituted or substituted; halides, heteroaryl radicals attached via nitrogen; amino and imino radicals which may be unsubstituted or substituted, etc.
Preference is given to phosphorus-containing benzoic acid derivatives of the formula IVxcex1 where L2=halogen (xe2x89xa1IV where R26=halogen), 
where the variables X, R1 to R4 and l are as defined under the compounds of the formula IV. Hal is halogen, in particular chlorine or bromine.
Preference is also given to the phosphorus-containing benzoic derivatives of the formula IVxcex2 (xe2x89xa1IV where R26=hydroxyl), 
where the variables X, R1 to R4 and l are as defined under the compounds of the formula IV.
Preference is also given to the phosphorus-containing benzoic acid derivatives of the formula IVxcex4 (xe2x89xa1IV where R26=C1-C6-alkoxy), 
where the variables X, R1 to R4 and l are as defined under the compounds of the formula IV and
T is C1-C6-alkoxy.
The particularly preferred embodiments of the phosphorus-containing benzoic acid derivatives of the formulae IV, IVxcex1 where L2=halogen, IVxcex2 and IVxcex4 with respect to the variables X, R1 to R4 and 1 correspond to those of the phosphorus-containing benzoyl derivatives of the formula I.
Particular preference is also given to the compounds of the formula IV where the variables have the following meanings:
R1,R2 are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, mercapto, C1-C6-alkylthio, C3-C6-alkenylthio, C3-C6-alkynylthio, amino, C1-C6-alkylamino or di-(C1-C6-alkyl)amino, where the alkyl, alkenyl or alkynyl radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfonyl, di(C1-C4-alkyl)-amino, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, phenyl or heterocyclyl, where the two lastmentioned radicals for their part may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1xe2x80x94C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
are phenoxy which may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl; or
R1 and R2 together form a xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94NR5xe2x80x94(CH2)mxe2x80x94NR5xe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94NR5xe2x80x94 or xe2x80x94Sxe2x80x94(CH2)mxe2x80x94NR5xe2x80x94 chain which may carry one to three radicals from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or phenyl, which is unsubstituted or partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1xe2x80x94C4-alkyl, C1xe2x80x94C4-haloalkyl, C1xe2x80x94C4-alkoxy, C1xe2x80x94C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R3 is cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, xe2x80x94P(xe2x95x90X)R1R2, phenyl or heterocyclyl, where the two lastmentioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R4 is nitro, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl or C1-C6-alkylsulfonyl;
R5 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy;
l is 0, 1 or 2;
m is 2, 3 or 4;
R26 is a radical which can be removed by hydrolysis.
Especially preferred are the compounds of the formula IV where the variables have the following meanings:
R1, R2 are hydrogen, C1-C6-alkyl, C1-C6-alkoxy or C1-C6-alkylthio, where the alkyl radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkoxy, C1-C4-alkylthio, di-(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
R3 is cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl or C1-C6-haloalkylsulfonyl;
l is 0.